FR2100681A1 - - Google Patents

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Publication number
FR2100681A1
FR2100681A1 FR7118932A FR7118932A FR2100681A1 FR 2100681 A1 FR2100681 A1 FR 2100681A1 FR 7118932 A FR7118932 A FR 7118932A FR 7118932 A FR7118932 A FR 7118932A FR 2100681 A1 FR2100681 A1 FR 2100681A1
Authority
FR
France
Prior art keywords
group
carbon atoms
formulμ
compound
general
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
FR7118932A
Other languages
French (fr)
Other versions
FR2100681B1 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE2025414A external-priority patent/DE2025414C3/en
Priority claimed from DE19712104580 external-priority patent/DE2104580C3/en
Application filed by Bayer AG filed Critical Bayer AG
Publication of FR2100681A1 publication Critical patent/FR2100681A1/fr
Application granted granted Critical
Publication of FR2100681B1 publication Critical patent/FR2100681B1/fr
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
    • C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
    • C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
    • C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/429—Thiazoles condensed with heterocyclic ring systems
    • A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/32—One oxygen atom
    • C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
    • C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
    • C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
    • C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
    • C07D499/68—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with aromatic rings as additional substituents on the carbon chain

Abstract

1301961 Preparation of ureido penicillins BAYER AG 25 May 1971 [25 May 1970 22 Aug 1970 1 Feb 1971 3 Feb 1971 9 March 1971] 16880/71 Heading C2A The invention comprises a process for the preparation of penicillins of Fomula (I) and salts thereof, which process comprises reacting a compound of Formula (52) or a condensation product of such a compound with a carbonyl compound, preferably acetone, of general formula (53) or a compound of general formula (54) or (55) at a temperature of -20‹ C. to +50‹ C. with a compound of general formula (57) or (58) or in a solvent and in the presence of a base when a compound of general fromula (52) or (53) is used, and in an anydrous solvent free of hydroxyl groups with or without the presence of a base when a compound of general formula (54) or (55) is used; and when a salt is derived converting the penicillin thus produced into the desired salt. In the above formulµ, A denotes a group of general formula wherein X is hydrogen or an alkyl, alkenyl, cycloalkyl or cycloalkenyl group with up to ten carbon atoms, or a vinyl, arylvinyl, mono-, di- or tri-haloalkyl, monoalkylamino, dialkylamino, monoarylamino or arylalkylamino group, or an alkoxy or aralkoxy group with up to eight carbon atoms, or a cycloalkoxy group with up to 7 carbon atoms, or an aryloxy group, or a group having one of the general formulae in which formulµ V is a divalent radical with one to three carbon atoms, n is 0, 1 or 2 and R 1 , R 2 and R 3 , which may be the same or different, each denote a hydrogen, chlorine, bromine, iodine or fluorine atom or a nitro, nitrile, dialkylamino, dialkylaminocarbonyl, alkanoylamino, alkoxycarbonyl, alkanoxyloxy, alkyl, alkoxy with up to 6 carbon atoms, sulphamyl or trifluoromethyl, Y is an alkyl, alkenyl, cycloalkyl or cycloalkenyl group with up to 10 carbon atoms, or a vinyl, propenyl, mono-, di- or trihalo alkyl group with up to 8 carbon atoms ; #Z- denotes a divalent group having one of the general formulµ in which n is an integer from 3 to 5 and the arrow of the divalent group Z means that the linkage of the two free valencies of the group #Z- with the nitrogen and carbon atoms of the group of general formula (3) is not arbitrary, but is orientated as indicated by the arrow; E denotes an oxygen or sulphur atom; and Q denotes a divalent radical ; particularly a radical having one of the general formulµ in which general formulµ G is a hydrogen atom or a C 1 -C 6 alkyl group, the arrow means that the linkage of the two free valencies of the group Q with the two nitrogen atoms of the group of Formula (4) is orientated as indicated by the arrow; and M is a group having one of the general formulµ In the above formulµ B denotes a phenyl group or a phenyl or thienyl group substituted by an alkyl, alkoxy or alkylthio group having 1 to 6 carbon atoms; and C* is a carbon atom which constitutes a chirality centre which can be in either of the two possible R- and S- configurations, R 4 , R 5 and R 6 are C 1 -C 6 alkyl groups and w is a halogen atom or an azide group. The invention also comprises D-α-(3- acetyl - 3 - methyl - ureido) - benzyl - penicillin, D - α - (3 - dimethylaminocarbonyl - 3 - methylureido) - benzylpenicillin, D - α - (pyrrolid - 2- on - 1 yl - carbonylamino) - benzylpencillin and D - α - (imidazolidin - 2 - on - 1 - yl - carbonylamino) benzylpenicillin and the sodium salts thereof. Phermaceutical compositions containing at least one of the above penicillins as antibiotically active ingredient have been prepared.
FR7118932A 1970-05-25 1971-05-25 Expired FR2100681B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2025414A DE2025414C3 (en) 1970-05-25 1970-05-25 Cyclic acylureidophenylacetamidopenicillanic acids
DE19712104580 DE2104580C3 (en) 1971-02-01 1971-02-01 Acylureidopenicillins

Publications (2)

Publication Number Publication Date
FR2100681A1 true FR2100681A1 (en) 1972-03-24
FR2100681B1 FR2100681B1 (en) 1974-10-18

Family

ID=25759178

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7118932A Expired FR2100681B1 (en) 1970-05-25 1971-05-25

Country Status (28)

Country Link
JP (1) JPS5538357B1 (en)
AR (2) AR195267A1 (en)
AT (1) AT307617B (en)
BE (1) BE767647A (en)
BG (1) BG23220A3 (en)
CA (1) CA943128A (en)
CH (1) CH562249A5 (en)
CS (1) CS171230B2 (en)
CY (1) CY829A (en)
DD (1) DD91497B3 (en)
DK (1) DK133679C (en)
EG (1) EG10856A (en)
ES (4) ES391532A1 (en)
FI (1) FI54484C (en)
FR (1) FR2100681B1 (en)
GB (1) GB1301961A (en)
HU (1) HU162205B (en)
IE (1) IE35311B1 (en)
IL (1) IL36905A (en)
KE (1) KE2592A (en)
LU (1) LU63203A1 (en)
NL (1) NL172660C (en)
NO (1) NO141164C (en)
PH (1) PH14794A (en)
RO (2) RO59157A (en)
SE (1) SE395896B (en)
SU (1) SU472507A3 (en)
YU (1) YU130271A (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4039673A (en) 1973-10-30 1977-08-02 Bayer Aktiengesellschaft Penicillins and cephalosporins and their production
DE2354219A1 (en) * 1973-10-30 1975-05-07 Bayer Ag BETA-LACTAM-ANTIBIOTICA, A PROCESS FOR THEIR MANUFACTURING AND ITS USE AS A MEDICINAL PRODUCT
GB1486349A (en) * 1974-11-28 1977-09-21 Bayer Ag Beta-lactam antibiotics process for their preparation and their use as medicaments
GB1584400A (en) * 1976-12-24 1981-02-11 Bayer Ag (2-oxo-imidazoliden-1-yl(carbonylamino)-acetamido-cephalosporins and penicillins
DE2658906A1 (en) * 1976-12-24 1978-07-06 Bayer Ag BETA-LACTAM ANTIBIOTICS, THE METHOD OF MANUFACTURING AND THEIR USE AS A MEDICINAL PRODUCT
CA1133896A (en) * 1978-05-26 1982-10-19 Nobuhiro Oi Penicillanic acid derivative and process for preparing the same
JPS5732289A (en) 1980-08-05 1982-02-20 Chugai Pharmaceut Co Ltd Alpha-substituted ureidobenzylpenicillin

Also Published As

Publication number Publication date
AR195267A1 (en) 1973-09-28
DK133679C (en) 1976-11-15
IE35311L (en) 1971-11-25
IE35311B1 (en) 1976-01-07
NO141164B (en) 1979-10-15
AR195946A1 (en) 1973-11-15
RO59157A (en) 1976-04-15
ES403126A1 (en) 1975-05-01
SE395896B (en) 1977-08-29
FI54484C (en) 1978-12-11
SU472507A3 (en) 1975-05-30
NO141164C (en) 1980-01-23
BG23220A3 (en) 1977-07-12
GB1301961A (en) 1973-01-04
NL172660B (en) 1983-05-02
DK133679B (en) 1976-06-28
FI54484B (en) 1978-08-31
FR2100681B1 (en) 1974-10-18
NL7107175A (en) 1971-11-29
BE767647A (en) 1971-11-25
CA943128A (en) 1974-03-05
HU162205B (en) 1973-01-29
KE2592A (en) 1976-01-09
ES403125A1 (en) 1975-12-16
PH14794A (en) 1981-12-09
YU130271A (en) 1982-02-25
RO62689A (en) 1978-05-15
EG10856A (en) 1977-05-31
CS171230B2 (en) 1976-10-29
DD91497A5 (en) 1972-07-20
CH562249A5 (en) 1975-05-30
NL172660C (en) 1983-10-03
IL36905A0 (en) 1971-07-28
ES403124A1 (en) 1976-01-01
IL36905A (en) 1975-11-25
ES391532A1 (en) 1974-10-01
JPS5538357B1 (en) 1980-10-03
LU63203A1 (en) 1971-09-01
AT307617B (en) 1973-05-25
DD91497B3 (en) 1988-01-27
CY829A (en) 1976-03-19

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Legal Events

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CD Change of name or company name
ST Notification of lapse